


Still Clueless

by Andromytta, Undici



Category: Clueless (1995), Supernatural
Genre: Copious 90s References, F/M, M/M, POV Alternating, POV First Person, POV Third Person, Underage Drinking, Unreliable Narrator
Language: English
Status: Completed
Published: 2019-06-17
Updated: 2019-06-17
Packaged: 2020-05-13 07:40:46
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 20,288
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19246789
Author URL: https://archiveofourown.org/users/Andromytta/pseuds/Andromytta, https://archiveofourown.org/users/Undici/pseuds/Undici
Summary: Take a stroll through the mid-nineties as we are reunited with the crew from Bronson Alcott High School after the wedding of Ms. Geist and Mr. Hall.Join Cher Horowitz and her friends: Sam Winchester, Dionne Davenport, Castiel Shurley, Murray Duvall, Dean Smith, Charlie Bradbury, and Summer Park as they navigate their senior year, with family changes, new friends, and coming outs.A sequel, of sorts, to that 90s blockbuster, Clueless, where Supernatural characters star as some of the beloved (and not so beloved) characters from the film.





	1. Still Clueless

**Author's Note:**

> When I was in college in 1990-something, every weekend my roommate and I would watch Clueless. It was our ritual. In a fit of nostalgia, I watched it again, only this time, with a firm Supernatural obsession, I thought to myself, "Self, what if Christian Stover was played by Castiel, and Elton was played by Dean Smith and his douchey attitude had a different motivation all together?" And hence, "Still Clueless" was born. I've been letting this percolate in the back of my mind for quite a while, and when this bang came around, it was the perfect opportunity to release it into the world. 
> 
> Special thanks to my amazing artist! Check out those 90s fashions! Fabu, right?

So, I’m starting my senior year at Bronson Alcott High School.  I’m sure it comes as no surprise that me and my crew plan to rule the school, despite all the changes we went through over the summer.  First of all, Sam Winchester and I are still dating.  He’s doing great; Daddy gave him an internship at his law firm, and is still trying to talk him into corporate law instead of environmental law.  Oh, and he’s helping me with my college applications.  Apparently, I should have had them done last year, but whatever.  Sam thinks I should major in business, because I’m really good at math, and then maybe I can help some nonprofit groups with their bookkeeping or whatever.  I was also thinking about PR, because how fun would it be to convince these big, rich businesses to help the less fortunate?  Sam thinks I’d be good at that too.

Tai and Travis surprised everyone by leaving Beverly Hills.  Don’t worry, they didn’t elope or anything like that.  Travis got this really great sponsorship for his skate boarding, and now they’re both travelling all over the country for like, competitions and stuff.  It sucks that they won’t be able to graduate with us, but it’s still pretty bitchin that they get to do that.

Dionne and Murray only broke up twice over the summer, which is a new record.  Of course, they’re still together and still bucking for most dramatic couple at Bronson Alcott high.  But they wouldn’t be them if they didn’t.

A lot of people took time over summer vacation to improve themselves.  Take Dean Smith, for example.  We used to be really good friends, until he broke Tai’s heart and sexually harassed me.  We realized he was kind of an asshole.  But, over the summer, this new girl, Charlie Bradbury, moved in next to him, and they started spending a lot of time together.  She’s been _really_ good to him.  Dean stopped drinking and started in AA.  He made amends to me and Tai.  Charlie has been great, and it’s nice to finally see Dean settled already.

What else happened?  Let’s see…  Oh yeah!  Remember Castiel Shurley, who I dated for all of half a second before I realized he was gay?  Well, he’s living with his father in Beverly Hills full time now.  His mom gave up joint custody when he came out of the closet to her over the summer.  It was awful.  I valiantly offered to go to Chicago to meet his mother and pretend to be his girlfriend, because she kept setting him up with the vapid, shallow daughters of her vapid, shallow friends.  She liked me so much that she tried to start planning our wedding!  Even though we’re both still in high school!  As if!  Even if Cas wasn’t gay, that was so not happening.  Unfortunately, she caught me on the phone with Sam, and that kind of blew it, especially when Naomi started saying disparaging things about my virtue.  Castiel got disowned by his mother because of me!  It’s a good thing she lives in Chicago and his dad lives here, because Cas needs me now more than ever.  He’s my best friend; it’s my job to take care of him.

Which is what I’m doing today.  With senior year fast approaching, we clearly needed new school clothes.  It was time to hit the mall!  I knocked on his door, and his dad answered the door.  I’m surprised they don’t employ a housekeeper.  I mean, Chuck Shurley is like, this really famous author.

“Hi Cher,” he said.  He was still in his open (yikes) bathrobe.  This did not bode well for Castiel’s condition.

“Hi Mr. Shurley.  Is Cas up yet?”

“How many times do I have to tell you?  Please, call me Chuck.”

“Ok, Mr. Shurley.”  My father always taught me to respect my elders.

He sighed heavily.  “Cas is in the living room.”

“Castiel, you look awful,” I said as I plopped down next to him on the sofa.  I didn’t see the point in lying to him.  Besides, when I was done with him, he’d be back to his old self, I was sure of it.  But now, his bright blue eyes were dull and lifeless.  His normally flawless style was…well, he was still his pajamas for crying out loud!  I mean, this was not the Castiel Novak I had spent several weeks pining over last year.

***

Castiel Shurley was your average high school senior, save for the fact that he was openly gay in high school in 1996.  At least it was high school in Beverly Hills, and his best friend was Cher Horowitz, the Queen Bee of Bronson Alcott High School.  It was both a blessing and a curse that he now lived with his dad, Chuck, full time instead of spending half the year with his mother in Chicago.  For the most part, he had a decent life.  An awesome BFF, and a hot boyfriend, what more could he ask for?

***

“Go away, Cher.”  Good grief, even his normally deep and growly voice was weak.

“I will not.  You are my friend.  My best friend, but don’t tell Di or Tai that I said that, and you need me now, more than ever.  So let’s get you showered, because, yuck, and get you out of this house!”

We went up to his room, and while Cas was in the shower, I picked out some clothes for him to wear to the mall.  It was really easy.  I mean, Cas has great taste and pretty much everything looks good on him.  I laid out his outfit just as he came out of his bathroom wearing nothing but a towel.    “You know, it’s insanely unfair that someone who looks like you bats for the other team,” I joked.

“What would Sam say if he knew you were staring at me like that while I’m dressed like this?”  Cas said.  At least he sounded like himself again.

“He’d probably say something like ‘You can look but you can’t touch. Hahaha.’”  I dropped my voice low to mimic Sam’s dorky voice.  “Ok, get dressed.”

“Um, leave?”

“Why?  You’re gay; it’s totally ok for me to be in here.”

“But you’re not, so it really isn’t.”

“Ugh, fine.  But you only have ten minutes, and then I’m sending in reinforcements,” I said, daring him to bail on me.  “And by reinforcements, I mean your dad!” I added as I slipped out the door.

Exactly nine and a half minutes later, Cas came down the stairs and into the living room.  “Alright, Duchess.  Ready to shop ‘til we drop?”

I was ecstatic.  It sounded (and looked) like my Cas was back! 

When we got out to his driveway, he asked whose car we should take (yes, I finally got my license, thank you very much).  I told him we should take my Jeep.  It can hold a lot more shopping bags than his…whatever it is.

“It’s a 1954 Nash Metropolitan.  I’ve told you that before, Cher.”

“Whatever.  It’s a cute car, and I’m sure the boys dig it.”

Cas rolled his eyes at me as we got into my Jeep.  He does that a lot.  I should probably be offended, but since it’s Castiel, I’m totally not.

We got to the mall and started shopping, and it was as if what was left of the black cloud hanging over Castiel’s head lifted.  Mission accomplished.  I mean, I know how much it sucks to lose your mom, but to have her purposefully disown you because of who you love?  That’s completely bogus.  And totally unfair to Cas.  If she lived in Beverly Hills, I’d make her a social pariah in thirty seconds flat.  I try very hard not to use the word “hate” towards anyone, but I hate Naomi Shurley with every fiber of my being.  She’s a horrible human being.

The food court was calling our names, so we took a break from shopping.  Who should we meet there but Dean Smith and Charlie Bradbury?  We’ve been running into them at the mall all summer.  Is that weird?  I mean, it _is_ the mall; it’s the happiest place on earth, so it shouldn’t be weird, right?

“Hi, Dean. Hi Charlie!” I greeted them with a smile.

“Hi you two,” Cas said, awkwardly.

“Hey, um hey.”  Apparently, Dean had become awkward when he became sober.

“Hi!” Charlie said enthusiastically.

“Coffee.  I’m going to get us coffee.”  Dean said before turning on his heel.

“He didn’t even ask what we wanted.” I said absently as I watched him scurry off.  The rest of us found a table and sat down.  Cas and Charlie didn’t really know each other, so it was up to me to keep the conversation flowing.  “So, Charlie, how do you like Beverly Hills so far?”

“It’s a lot different from Kansas, that’s for sure.  But Dean has made the transition easier,” she said with a smile.

“You’ve been a good influence on him, too.”  I had to give her props.  “I mean, we all remember what a mess Dean was last year, especially after his break up with Vallette.”

“Yeah, he’s a sweet guy.” 

Before I could respond, Dean came back with the coffees.  Well, two coffees.  He passed one to Cas.  “Cappuccion, extra sweet, extra foam, right?”

“Yes.  Thank you, Dean.”

He sat down in the only empty seat at our tiny table, between Charlie and Cas.  Charlie smacked him on the chest.  “You forgot our coffees, doofus.  Come on, Cher.”  Before I could protest, Charlie was pulling me out of my chair by my arm and leading me to the coffee shop.

“That’s so weird that Dean got coffee for Cas, but forgot to get yours,” I said as we waited in line.

“Um, yeah.  Dean’s great, but sometimes he can be a bit absent minded.  It’s ok though, gives us a chance to have some girl time!”

Well, it was hard to argue with someone who was that enthusiastic.  I decided to change the subject.  “Charlie, you should let me give you a makeover!  Let me de-flannel you a little bit!”

“Thanks, Cher.  That might be fun, sometime.”

Before I could pull out my PDA and lock in a time, we were at the front of the line.  “Iced mochaccino, please,” I ordered, then gestured for Charlie to do the same.  “And whatever she wants.”  Since her boyfriend didn’t buy her coffee, it was the least I could do.

“Triple red eye,” she ordered.

“Hey, that’s what I drink too,” a voice said behind us.  A voice I knew very well. 

I turned around with a big smile on my face.  “Sam!  What are you doing here?  I thought you were busy at Daddy’s office all day?”

“He gave the interns a half day off today.  I’m not sure why.  He must be getting soft in his old age.” I slapped him on the arm for that.  Daddy was not getting old.  “Anyway, I thought I’d come see what you were up to.  Why am I not surprised that you’re here?”  He hugged me, picking me up off the ground.  I really do need to be 5’10” like Cindy Crawford if I was going to be able to kiss my 6’4” boyfriend and still keep my feet on the ground.  Even in my six inch platforms, he was still half a foot taller than me.  It was ridiculous.

“Well, Castiel and I need new clothes for school.  I’m assuming that’s why Charlie and Dean are here too.”   The barista had our drinks ready and we headed back to the table.

“Yep, that’s why we’re here,” Charlie confirmed.

When we got back to the table, Sam took my vacated chair, leaving me no choice but to sit in his lap.  I live a tough life sometimes. 

“I hope we’re not interrupting anything,” Charlie said once we sat down.  I don’t know what we could be interrupting, it’s not like Castiel and Dean were friends or anything.  Even if the four of us have managed to have coffee at least twice a week all summer long.

“Oh, Charlie, I’m sure we’re not interrupting,” I said.  “So, when are we going to do your makeover?”

“You’re letting Cher give you a makeover?” Dean asked.  I’m not sure I liked the tone of his voice.

“Well, yeah.  I should try to de-flannel her a little bit if she’s going to keep up with you, Mr. Super Put Together, with your suspenders and fancy dress shirts.”  I explained.  I mean, it was simple.

“I-I never exactly agreed,” Charlie said (even though she totally did).  “I mean, I did say it might be fun…”

“Charlie, are you ducking me?  It sounds like you’re ducking me.”  What?  I’m allowed to call her out.

Cas looked Charlie right in the eye, and said with all seriousness, “It’s easier if you just say yes.  Her main thrill in life is a makeover.  It gives her a sense of control in a world full of chaos.”  Did he and Dionne rehearse that?

I took her hands and said, “Look, if you hate anything, or everything I do, you don’t have to keep it.  If you really are that uncomfortable with your new look, you can go back to being the flannel bound goddess you already are.”  Sam gave me a little squeeze from behind.  I’m sure he’s totally proud of me for not trying to turn everyone into my clone.  Like he accused me of doing with Tai last year.

“Ok, fine,” Charlie relented.  “How about next weekend?”

I shook my head vehemently, sending my blonde, multi tonal locks flying.  “No!  We should do it on Saturday.  There’s that huge pre-back-to-school party, and we can get you looking super-hot for it!”

Charlie shrugged.  “Ok, fine.  Saturday it is then.  But, I get to veto anything I don’t like, right?”

“Of course,” I nodded.  I mean, we do live in a democracy, right?  Besides, I’m sure she would love everything I’d come up with.

“Cher, if you’re finished shopping, can we go?”  Sam asked out of nowhere. 

“Um, yeah, I guess.  Cas, are you done?”  I asked.

“You guys can go.  We can take Cas home.  Right, Charlie?”  Dean offered.  Also out of nowhere.

Charlie nodded at him.  “Sure we can Dean!”

“That’s really decent of you guys.  Thanks.”  I looked up at Sam.  “Yeah, I think I’m finished.  We can go.”

Sam collected all of my bags and we made our way out to the parking garage to my Jeep.  Apparently, he had someone drop him off, so his car was still at Daddy’s office.  Of _course_ Sam insisted on driving.  I relented, because who could resist that puppy dog face?  As soon as we pulled out of the parking lot, Sam said what was really one his mind.

“How can you still hang out with that Dean guy?”

“What do you mean?  He’s my friend.”

“After what he did to you?  I don’t like him.”

“Sam, he’s with Charlie now.  And he full on made amends.  He’s a better person now, and we should be totally supportive of personal growth, right?”

“Fine, I guess.”  He said.  Although he didn’t sound fine.

Saturday rolled around, and I was stoked to give Charlie a makeover.  I just knew there was a full-on Betty underneath of all that flannel.  And I was going to excavate her.  I called Dionne to see if she wanted to come over and help, but apparently she and Murray had some big plans.  So, I called Castiel.  He had plans too.  Which was really weird, because he didn’t really know many people in Beverly Hills.   Sam was also conspicuously absent from the manor too.  Weird, he was practically part of the furniture at this point.  Like, why was he even still paying for that apartment near campus?  Anyway, I digress.

It didn’t matter that no one was here to witness the magic I was going to work on Ms. Charlie Bradbury.  At the party, everyone would be way impressed to see the goddess I was about to unleash.  There’s an uber hottie in there, I just know it!  The doorbell rang, and with a little squeal, I opened the door. 

“Hi Charlie!  Please, come in!”  I linked my arm in hers and ushered her in.  I led her up to my room, and we started with her hair.  I was running my fingers through her bright red curls, trying to see what I could do with it.  “Is this your natural hair color?”

“Well, yeah…why?”

“Charlie, do you have any idea how lucky you are?  This color is _so_ in right now!  And almost impossible to get from a bottle.  And here you are, growing it right out of your head!  And these curls are great.  We can probably leave it alone, except maybe put a texturizer in it to make your curls stand out, give them more definition, and make them sleeker.  Maybe put it up on one side with a cute hair clip.  How does that sound?”

I have to admit, Charlie did look just a bit apprehensive.  “Good, I guess.”  I would not be dissuaded, however.

“Ok, so the next thing is to pick out a bitchin outfit to wear to the party tonight.  I know you and Dean are a thing, and you don’t want to make him look bad, right?  Dean Smith is one of the most fashion forward guys at Bronson Alcott high, and as his companion, it is your responsibility to also look the part.”  I explained, trying to expound upon the importance of wardrobe at all social functions.

“Alright,” Charlie said slowly.

I opened my closet door and turned on the rotating racks.  “Ok, Charlie, look through here and see if anything speaks to you.  Because along with being fashion forward, you still need to be as comfortable as possible in your binding party clothes.”

Charlie took her time perusing my extensive wardrobe.  I understand, picking out party attire was a very serious affair.  I spent an hour and a half this morning deciding what I wanted to wear to the party myself, and I know my wardrobe.  Charlie actually sounded excited when she found something she liked.

“Oh!  Can I wear this?”  She pulled out a shiny blue number with cap sleeves, which I may or may not have purchased with her in mind when we were all at the mall the other day.

“Absolutely!”  I exclaimed happily.  “That will look dope on you!  Why don’t you try it on?”

With a bright smile, Charlie went into my bathroom to change her clothes.  I felt this immense satisfaction, making another person happy through fashion.  Admittedly, Charlie would likely revert to her normal style after tonight’s party, because she wasn’t the type who would just bow down to someone else’s influence (which is probably why she and Dean worked so well together) but for tonight, it was nice to see her experimenting with something new.

She came out and did a little twirl.  That dress was righteous.  It clung to her curves in all the right places.  Dean Smith was not going to know what hit him.  When he picked up his girl tonight, and saw her like that, well, I wouldn’t be surprised if his eyes bugged out of his head like a cartoon character.  “You look fantastic!  That dress is perfect for you.  In fact, why don’t you keep it?”

“But Cher, it’s yours.  And it’s not really my style.  I mean, it will be fun to wear to the party, but I don’t really think I can keep it,” Charlie protested.

“Nonsense.  It’s yours now.  Even if it’s not your normal style, you should still have it, wear it when you feel like being a little bit different, you know?  Besides, as you can see, I have plenty of clothes.”

“Wow, thanks Cher.”  Charlie said.  “You know, you’re not what I was expecting.  When I first met you, I thought you were sort of ditzy and kind of selfish.  No offense.” 

The way Charlie smiled at me, I knew she didn’t mean anything by it.  Besides, she wasn’t totally wrong.  “Well, you’re not totally wrong.  I used to be a little bit shallow.  But, we learn and we grow, and we should support positive growth in the people we love.  Which is why I’m so grateful that you came into Dean’s life.  He was such a mess last year, and did things I’m sure he’s not proud of.  But you really turned him around.”

“Cher, you give me too much credit.  I mean, yeah, I did support him and helped him get into AA.  But those changes, he did them all himself.  He wanted to be a better person.  I just…gave him a nudge.”

“Well, whatever it was, it’s working.  Now, let’s find you shoes and do your makeup.”

Charlie left my house with her hair done, her makeup on, her dress and shoes in appropriate bags, and a smile on her face.  I couldn’t wait to see the look on Dean’s face at the party tonight.  They were going to be the hottest couple at the party!  And I was glad it was going to be them, since Sam and I rarely bucked for hottest couple.  I mean, speaking of someone who needed some serious de-flannelling.  I mean, I love Sam, but he really needs to let me dress him once in a while.  Especially when he’s escorting me to parties.  Although, granted, most of the time it was just me and Cas going to the parties.  And we did look hot together, even if we weren’t together-together.  You know?

Tonight…was the exception.  Imagine my surprise when Sam not only agreed to go to the party with us tonight, but he dressed the part.  He was wearing a very well fitting charcoal suit, crisp white shirt, and dark maroon tie.  The tie just happened to match the dress I was wearing tonight.  How did he figure that out?  He really is super smart.  And I didn’t even dress him!

“Sam, you look great.  I always knew there was a Baldwin in there somewhere,” I said as I stood on my tip toes to kiss his cheek.

“Thanks,” he said, an adorable blush painting his cheeks.

“So, what brought all this on?  You usually blatantly refuse to budge on your, um, inspired fashion choices.”

“You said that after doing your makeover that Charlie and Dean will be the hottest couple at the party.  Well,” he leaned down and whispered in my ear, “I think we can beat them.”

His lips close to my ear may have made a tiny shiver sneak down my spine, but it wasn’t enough to keep me from saying, “So, this is just about you wanting to beat Dean?”

“No, I just wanted to make you happy,” Sam said sheepishly.

“Sam, you always make me happy.  You don’t have to wear fancy clothes just because I enjoy seeing you in them.”

“So, you enjoy seeing me like this?”  He smiled brightly.

“Very much so.  Now, where is Cas?  We need to get going.”

As if he was reading my mind from afar, the doorbell rang.  Per usual, Castiel looked smokin’ hot.  He was wearing a white, orange, and blue plaid suit with a matching powder blue shirt that really brought out his eyes and his ever present fedora.  After complimenting each other on how hot we all looked, we piled into Sam’s car.  Sam said it would be much safer if he drove us.  I guess he knew us well enough by now that we wouldn’t let a little thing like being under 21 keep us from indulging.  As long as he didn’t tell Daddy, it would be fine though.

The party was in full swing when we got there.  I can’t count the number of times I’ve had to explain to Sam how much better it is to arrive fashionably late.  I was pretty sure we were the last to arrive.  Cas took my arm and attempted to lead me out onto the dance floor when Sam stopped him.

“Can I dance with my lady tonight?”

“God, Sam, could you be any more cheesy?”  I teased, but I was smiling.  He was such a dork, but he was my dork.

“Of course,” Cas released my arm.  “I’ll catch you later, Duchess.”

“Bye,” I waved at him as Sam led me onto the floor.

We were dancing for a few minutes…well I was dancing, Sam was kind of jumping around like a spaz…when I looked towards the door.  “Oh!  Look, there’s Dean and Charlie!  Look at her!”  Charlie was wearing the dress I gave her, and still in full hair and makeup from earlier.  Color me surprised, I really thought Charlie would go back to her normal style.  She looked great, party perfect.  But…not like herself.  Is it possible that trying to change someone in a positive way might not actually be so positive?

“Wow, she does look amazing.”  Sam said in awe.  I wasn’t at all jealous.  I was fully aware that Sam only had eyes for me.  But it was still nice for him acknowledge someone else’s beauty.

“Sam, I should make the rounds, say ‘hi’ to everyone.  You want to come?”

“No, thank you.  I’ll just grab us some drinks.”

“Ok,” I said, once again standing on my tip toes to kiss his cheek.  How did I get so lucky to land such a great and considerate guy?

I found Cas and together we made the rounds.  Eventually, we found Dean and Charlie. 

“Charlie, you look great,” Cas said.

“Yeah, I still can’t believe she let Cher give her a makeover.”  Dean chuckled.

“You really do look amazing, Charlie,” I said.  “But I totally understand if you choose not to dress like this every day.”

“Thanks, Cher,” Charlie said.  “I do really like this look, but it’s really not me.  I mean, it’s great for parties, but it’s really not something I’d want to do every day.”

“Well, every day Charlie is beautiful too!”  I said with a smile.  She and Dean were such a cute couple.  “Are you guys going to dance?”

“I don’t think so,” Dean started.

“Oh, come on!  Cas and I were just about to go out there.”

“Well, in that case, how can I say no?”  Dean said, and took Charlie’s arm, following us out onto the floor.

As we danced, the four of us seemed to intertwine pretty regularly.  Charlie and I ended up dancing together, so did Dean and Cas.  I had to give Dean snaps for not freaking out about dancing with an openly gay man.  Most guys these days were not that open minded.  I mean, Sam’s totally open minded, but he’s not a normal guy.  At one point, even Dean and I danced together, and it totally wasn’t awkward at all.  He kept his hands appropriate for the dance, and didn’t do anything that would make his girlfriend or my boyfriend uncomfortable.  Charlie really has been a good influence on him.

We were having a blast.  I kind of lost Sam while Cas and I were making our rounds, so was completely surprised when he made his way back to the dance floor and swept me away.  “Sam!  I was dancing over there.”

“Yeah, with that Dean guy.”

“Sam, you know, you really have to get over this whole Dean thing.  I mean, if _I’m_ over it, you should be too.  We’re friends now.  Just friends, and he knows what he did was wrong.  He knows I’m with you now, and he’s with Charlie.  There is absolutely nothing to worry about.”

“I still worry, ok?  I’m allowed.  That guy assaulted you and left you to get robbed in a parking lot!”

“Yeah, but in teenage time, that was like a thousand years ago.  I can forgive and forget.  You should, too.  Besides, if it wasn’t for that night, I might not ever have realized just how cute you are.”  I smiled at him, and when he smiled back, I knew the subject was dropped.

At one point during the party, I had completely lost track of Cas, only to find him later with Dean and Charlie.  He seemed fine, so when Di and Murray initiated their typical party drama, I felt totally ok leaving him alone to check on Di.  I don’t even know what the drama was about this time, but Dionne ended up riding home with us instead of Murray, so it must have been bad.  Dean and Charlie ended up taking Castiel home.  They seemed to be doing that a lot lately.  Was I failing in my best friend duties?  Should I have chosen Cas over Di?  I mean, he seemed to be totally ok, while Dionne clearly needed me, so, I did the right thing, right?

Before I knew it, it was the first day of school.  Senior year!  I was excited, but also a little nervous.  Sam said that if I wanted to get into a good college and do really well, I had to buckle down and really do the work required of me this year.  He said that in college, you can’t really argue you way to better grades.  If I couldn’t argue my way to better grades, what would I do?  I guess I needed to do the actual work, call it practice for college.  Ugh.  This was going to be a different kind of year for me.

I was, quite surprisingly, stoked for the new school year.  Dean Smith and I renewed our friendship, despite his deplorable behavior after the Val party last year.  His new girlfriend, Charlie Bradbury, was doing wonders for his demeanor.  I knew all he needed was to be settled already.  Speaking of Charlie, she was wandering around the quad looking a little befuddled.

“Charlie!”  I called out to the perky red head.  “Charlie!”  I waved her over.  “You look distraught.  What’s wrong?”

“I just…I don’t know what to make of this school.  You guys actually have a cappuccino bar.  I mean, it’s awesome, but I’m definitely not in Kansas anymore.”

“Oh, well, this is really good school.”

Dionne, Castiel, and I walked down the halls like we owned the place.  Which, in a way, I suppose we kind of did.  It was a total bummer that we didn’t have any classes together this year. We were the most popular kids in school, along with Dean (and by extension, Charlie), Murray, and Summer.  Tai and Travis would have been part of our group too, if they weren’t on the east coast somewhere with Travis’s skate tour.  To no one’s surprise at all, Charlie was back in her typical flannel and jeans ensemble.  But you know what, on her, it worked.  Weirdly enough, she didn’t look totally out of place next to Dean in his suspenders and slacks.  Somehow, they fit.  It was amazing.  Maybe this year would be different, but I’m sure it would still be bitchin.

Time was flying by.  I was working super hard on my classes, taking care of Cas (who was still having issues due to his mother abandoning him) and spending time with Sam.  Before I knew it, the semester was wrapping up and report cards were coming out.  My eyes were bugging out of my head.  My lowest grade was a B minus?  That never happened!  In semesters past, I’ve always had to argue my way up to a B minus.  Except for in math.  I always got an A in math without having to argue it better. 

I was staring at my grades in disbelief when my phone rang.  “Di!  How did you do?”

“Mr. Hall lowballed me again.  I got a C.  How did you do?”

As we were talking, we met up in the hallway.  “The lowest grade I got was a B minus, and that was in gym.”

“I don’t think Ms. Stoger ever forgave you for pointing out how useless physical education in this school is.”

“You’re probably right, Di.”

“I can’t believe you didn’t have to argue your way to those grades this year!”  Dionne was as surprised as I was.

“I know!  I guess Sam was right, if I put the work in, I get the rewards.”

“So, do you want to celebrate?  Go to the mall, have a calorie fest, and watch the new Leonardo DiCaprio movie?”  Dionne asked.

“Oh, Di, you know I would love to, but I kinda promised Cas we would hang out tonight.  It’s the six month anniversary of his mom kicking him out.  He needs me.”

Dionne’s look turned from bright to dark.  “You know what, Cher, it’s always something with you!  You either need to study, or Sam is helping you with your college applications, or Cas needs you because his mom dumped him.  You never have time for me anymore.  You know, Cher, Cas isn’t the only one who needs you!  I’ve been trying to spend time with you all semester, and you always blow me off.  So you know what, Cher, I’m done!”  She stormed off down the hall before I had a chance for a rebuttal.

Was it true?  Was I neglecting my oldest friend for my boyfriend and my gay best friend?  Have I just completely abandoned Dionne?  What kind of person does that?  I guess I wasn’t as self-improved as I thought I was.  I stomped off down the hall in the other direction.  I had to figure out a way to make this up to Dionne.  I just didn’t know how.

A couple of days later, it hit me, I knew how to at least get Dionne to talk to me.  I waylaid her on the way to seventh period.  “Hey, Di!  Let’s ditch and go hit the mall!”

“You want to ditch class?  I thought the new and improved Cher Horowitz didn’t ditch class anymore.” Dionne had every right to snark at me.

“Yes, that’s true, but the new and improved Cher Horowitz isn’t exactly ‘improved’ if she doesn’t make time for her best friend.  Come on, Dionne!  You were right, I have been neglecting you, and I have no idea what’s going on in your life right now!  Let’s go, let’s get caught up!”

“Ok, fine.  I didn’t really want to go to PE anyway.”

“You never do,” I said with a smile as I led her off campus.

We went to the mall and we easily fell into our old patterns.  It was the best!  I didn’t realize how much I had missed Dionne until there we were at the mall just hanging.  So, I was going to have to work a little harder to make up for missing class.  Who cares?  My relationship with Dionne was at least as important as my grades.

Of course, we had to stop at the food court for some caffeine before we continued shopping.  We totally ran into Dean and Charlie.  Who knew?

“Dean, Charlie.  We have to stop meeting like this!”  I said jokingly as we all got our coffee and took a seat at one of the tables.  I turned to Dionne to explain.  “All summer, every time I brought Cas here to cheer him up, Dean and Charlie would always be here too.”

“That’s uncanny,” Dionne said, sounding a little irked.  I guess she didn’t like having our time interrupted…or maybe she just didn’t like me talking about Cas.

“Speaking of, is Cas here with you?”  Dean asked.

“Nope,” I said.  “It’s just a Cher and Dionne day,” I explained.

“Oh,” Dean said.  Did he sound disappointed?  Why would he be?  Were they really becoming such good friends?

“Well, we should let you get back to your Cher and Dionne time,” Charlie suddenly said.  “Come on, Dean.”

“Oh, ok,” Dean said.  I still swear he sounded upset.  I can’t fathom why.  I wonder if he and Charlie are having problems.

When we were finally alone, Dionne turned to me.  “Listen, Cher, there’s something I’ve been dying to tell you, but you never seemed to have the time…”

“Oh, Dionne!  I’m so sorry I’ve been neglecting you!  I promise, I’m going to try really, really hard to be a better friend from now on!”

“No, Cher, I know.  You tend to get wrapped up in your projects, and with Castiel’s mom just abandoning him like that, well, he’s a pretty big project.”

“So, do you forgive me?”  I gave Dionne my most sincere look.

“Of course I do.  But, listen, I really need to tell you something.”

“Of course, what is it?”

Dionne took a deep breath and flipped her braids over her shoulder.  A huge smile broke across her face.  She held her left hand up to me and said, “Murray proposed to me!  Murray proposed to me!”

“What?!?”  I exclaimed as I grabbed her hand.  “Whoa!  That’s quite a rock!  Is that a Jean Paul Gautier?”

“Of course it is.  Do you think I would have said yes to anything less?”

“Of course not!  Oh, Di!  I’m so happy for you!”  I stood up and gave her a giant hug.

“Really?  You are?  You’re not going to give me some lecture about how we’re just in high school and way too young to make this kind of commitment?”

I sat down and took a deep breath.  I turned to Dionne and put my most serious face on.  “Dionne, if it was anybody else, I might question it and make them pause to consider the fact that they are still in high school.  But you and Murray, well, you’ve been together since ninth grade.  You’ve been through a lot together, you’re going to the same college, and, I assume, you’re not actually going to get married until after college.”

Dionne smiled brightly at me.  Clearly she was pleased that I still know her so well, despite our lack of hanging out.  “Yes!  How did you know?”

“Well, you have always expounded on the merits of a long engagement.”

“But how did you know about me and Murray getting into the same school?”

“Oh, well, Murray and I have English Lit together, and he was very excited to announce to the whole class that you two would be going to UCLA together!”

She smiled softly.  “Murray really is great, isn’t he?”

I nodded.  “Yes.  Despite the manufactured drama in your relationship, it’s absolutely clear that you and Murray are majorly, totally, butt crazy in love with each other!”

Dionne squealed and hugged me.  “I’m so glad you’re happy for us!  I’m really happy, Cher, and I’ve been _dying_ to share my news with you!”

“I really am, so happy for guys!” I hugged her tight.  “And I promise to be more available for you in the future!  I’ve missed you, Dionne!”

“I’ve missed you, too!”

We finished our coffee and continued shopping until it started to get late and our parents called telling us to come home for dinner.  Dionne invited me over, and I accepted, telling Daddy I’d be going to her house for dinner.  I promised not to be gone too late, since I had homework to do, but Dionne and I needed this.  We needed to have a friendassance.

A few days later, Di and I were having coffee on the benches in the quad during study hall when Murray found us.  It was the first time I’d seen him since Dionne told me their big news.  I immediately jumped up from the bench to give him a big hug.  “Congratulations!  I’m super stoked for you guys!”

Murray returned the hug and looked at Dionne.  “So, I guess you finally told her.”

“I did.  As you can see, our friendship has been renewed.”

Murray sat down on the bench next to Dionne and I sat on the other side of her.  As we were chatting, Charlie and Dean strolled by.  “Hey you guys!”  I shouted and waved as they walked by.

“Aren’t they the cutest couple?”  I said once they were out of earshot.

“Who?” Murray asked.  He seemed confused.

“Dean and Charlie,” I said.

He laughed.  “Charlie Bradbury and Dean Smith?  They’re not a couple.”

“What do you mean?  Look at them.  They’re totally in love.”

Murray laughed again.  “I hate to burst your bubble, but there is no way those two are a couple.”

“What makes you say that?” I asked.

Murray just gave me that look he gives me when he thinks that I’m totally clueless.  “Your girl Charlie is a carpet muncher.”

“What?” Dionne and I asked.

“She’s a flannel wearing, Ellen watching, Melissa Etheridge listening lover of the female form!”

“Uh-uh!  No way!  Not even!”  I protested.  I was getting this weird sensation of déjà vu. 

“Yes, even!  She’s gay!”  Murray exclaimed triumphantly.

“She does wear a lot of flannel, Cher.  And she didn’t even stick to your makeover.”

“Oh my God!  I’m totally buggin’.  Oh!  I have to tell Dean!  I’m sure he doesn’t know.”

Dionne patted my arm soothingly.  “Why do you have to tell him, Cher?  How is it your responsibility?”

“I know it’s not.  But he’s been doing so well.  You guys remember how he was after his break up with Vallette.  And then I broke his heart.  And now this.  I’m not sure he can take one more hit.  I should tell him.  Break it to him gently so that he won’t go spiraling out of control again.”

“You’re a really good person, Cher,” Dionne said softly.

“How can he not know?” Murray asked, unbelieving.

“We didn’t know,” Dionne said.

“Yes, but, no offense Baby, but you two have horrible gaydar.”

“He’s not wrong, Di.”  I said.  “Remember when I thought I was going to have sex with Castiel?  Neither of us expected him to be gay.”

Dionne shrugged.  “I guess.”

I spent the rest of the day in a daze.  Another year older, and I was still utterly, totally, and completely clueless.  Charlie Bradbury was gay?  That would break Dean’s heart.  Someone had to tell him.  I suppose, after everything we’ve been through, that someone would have to be me.  Just the thought of it weighed heavily on my mind.  I had to figure out the right way to tell him, I couldn’t let him fall off the wagon after all.  Winter break was about to start, so this might be a good time to tell him.

***

What Cher didn’t know was that Dean Smith was well aware of Charlie Bradbury’s not so hidden sexuality.  In fact, it was Charlie who helped Dean come to terms with his own.  Even if Dean wasn’t ready to be open about it, he was finally ready to admit to himself (and to Charlie) that he was, in fact, very much into dudes.  One dude in particular had specifically captured Dean’s attention; one Castiel Shurley.

Unfortunately, Dean’s unwillingness to come fully out of the closet was a big source of dissent in their budding relationship.  Castiel was very into Dean, too, but after what he went through with his own family caused Castiel quite a bit of distress when he couldn’t even bring his boyfriend home to meet his (very accepting) father.  Hell, he couldn’t even tell his best friend he was in an important relationship because Dean was terrified that the rest of the school would find out.  For the sixth time since they started dating toward the end of summer vacation, Castiel Shurley broke up with Dean Smith.  There was only one way he could safely deal with his misery.

Technically, he wasn’t old enough to drink, but this particular bar rarely carded anyone.  It catered to the college crowd, and this particular bartender, Benny, had a bit of a thing for Cas.  If he thought Cas was in college, well, Cas never bothered to correct him. 

Since he and Dean had yet another fight, Cas started immediately with Scotch.  Benny just kind of squinted at him, but filled his glass. “Get into another fight with that boyfriend of yours?”  Benny asked after Cas’s third drink.  He laid on his Cajun accent extra thick to draw Cas out of his shell.

“Yeah.  He doesn’t want to go out in public with me because he’s too scared to come out of the closet.  I don’t know what he’s so scared of.  It’s not like his parents would just ditch him.  My mom disowned me, but I’m still out and proud.   It’s not like anyone at school would ridicule him, either.  I don’t know if he’s ashamed of who he is, or if he’s just ashamed…of me…”  Cas got really quiet for that last part and slid the glass away.

“So why don’t you just break up with him, if it’s this hard?”

“Because he’s so beautiful!” Cas whined before dropping his head to the bar.

Benny made a sympathetic sound before refilling Castiel’s drink.  “You do know there’s more to dating someone than just how beautiful they are, right?”  Not that Benny should have been surprised that was a deciding factor on Cas’s part.  This was Beverly Hills, after all.

Cas picked his head up and nodded gratefully at the bartender for the fresh drink.  “I know that.  But it is an overwhelming part of his personality.”  Castiel chuckled.  “Dean really is more than just a pretty face though.  He’s smart, he’s _very_ charming, and he’s a fantastic kisser.  He’s just got this one teeny tiny flaw.”

“Yeah, the kind of tiny flaw that means you’ve got to keep your relationship on the down low.  That’s just not fair to you, brotha.”

“I know, you’re right,” Castiel sighed.  “But I love him.”

***

I woke up the first day of winter break determined to tell Dean the truth.  After all, I know very well what it’s like to date someone who was really not into you.  I would draw on my own experience with Castiel to tell Dean about Charlie.  But…I should probably get Cas’s permission first.  After all, it’s not right to just tell someone else’s business….Yes, I get the irony of that, since that’s what I’m doing to Charlie.  Except not really, because it’s Dean’s business too!

After spending just a couple of hours in my closet trying to pick the best “breaking bad news to one of your dearest friends” outfits, I headed over to see Cas.  What I found put any and all thoughts of talking to Dean on hold.  Clearly Cas was having another one of his depressive episodes because of what happened with his mom.  He was laying on the sofa, still in his party clothes from last night (weird, he didn’t invite me to any party) and he was all but passed out.  Poor guy!  Clearly he needed me, immediately.

“Castiel Shurley, what is going on here?”  I asked as I gently nudged him awake.  I was totally gentle, I promise.

“Unghhfff.”  He groaned from underneath the throw pillow covering his face.

I chuckled at him.  “Dude, that’s not a word.”

He pulled the pillow from his face and sat up slowly.  He glared at me, he actually glared at me!  “Yes, it is a word.  It’s hangover for ‘Go away and leave me alone, Cher.’”  Then, he smirked.

“Ha ha.  Very funny.”

“What are you even doing here?” he asked grumpily.

“It’s the first day of winter break!  Let’s go out and play!”  I smiled brightly at him.

“I think I’ll just stay here and bask in my own misery, if it’s all the same to you.”

“It’s not.”  I nudged him with the pillow he had discarded.  I continued nudging him until he got off the couch.  “Good.  Now that you’re vertical, go take a shower.”

He scowled at me again.  “You’re not the boss of me.”

“Oh yes I am.” I nodded to emphasize my point.

“You know, Cher Horowitz, one of these days, I’m going to kill you in your sleep.”  Castiel glared at me again, but at least he started heading up the stairs.  Supposedly to shower.  I followed him, just to be sure.  “You’re not actually going to follow me into the shower, are you?”

“Ew.  As if!”

“Good.”  He slammed the door.  Right in my face!  How rude!

After a much longer shower than was probably necessary, Cas came out wrapped in his favorite towel.  I, of course, already had a stunning outfit laid out for him.  It wasn’t long before we were in his car cruising to the mall.  He was very insistent about driving today, and who was I to argue?

It was halfway through winter break before I finally had a chance to talk to Dean.  We were at a party at Summer’s house, just hanging out, you know, dancing, drinking, smoking, and in walked Bronson Alcott’s newest power couple, Dean and Charlie.  He looked so happy.  I really didn’t want to break his heart, but I knew what I had to do.  Once the new arrivals made their rounds, I excused myself from my crew (who at this point was just me, Summer, and Cas.  Dionne and Murray were off being dramatic again) and made my way over to Dean.

“Hey Dean, hey Charlie!”  I said amiably.  Then, in what I think was a super smooth transition, I said, “Oh my God!  I love this song!  Come on Dean, dance with me!”

I dragged him onto the dance floor and started dancing when he looked down and me and said, “But Cher, you _hate_ this song.”

When I realized what was playing, he was right.  I really did hate this song.  Guess there was no choice but to spit it out.  “You’re right.  I do hate this song.  But I just needed to talk to you alone.”  I looked at him with imploring eyes.  I even batted my eyelashes.

“Why?  Cher, what’s wrong?  Is it Cas?  Is he ok?”  Dean’s voice got a little high pitched, and he said all of that in one breath.

“Yeah, Cas is fine.  Why are you asking about Cas?”  I asked.  That was very confusing.

“Oh, um, no reason.”  Dean said awkwardly.  “So, what’s up?”

I took a deep breath and steeled myself.  “It’s about Charlie.”

“What about her?”  Poor Dean, he looked totally unconcerned and nonchalant.

“Dean, Charlie is a lesbian.”  It was best to just rip the Band-Aid off, right?

Dean started laughing.  He actually started laughing.  “I know that, Cher.”

“You do?” I asked.  This time my voice pitched higher.

“Uh, yeah.  She is my best friend.”

“But I thought she was your girlfriend.”

“Um…not exactly.”  Dean sighed and dropped his head to rest on top of mine.  “Listen, Cher, as far as anyone needs to know, Charlie is my girlfriend.  You see, there are things you don’t know.  Things only Charlie knows.  So if you could just keep this between us, I’d really appreciate it.”

I squinted at him in confusion.  “Keep what between us?”

“Exactly.” He said, as he spun me around the floor and deposited me back with my crew.

“What was that about?” Cas asked.  He sounded like he was accusing me of something.

“Nothing, I just wanted to dance with Dean.  This is a great song!”  I said, and I was the picture of innocence.

“You hate this song,” Summer pointed out.  I glared at her.

“Maybe it’s growing on me?” I said.

“As if,” Summer and Cas sniffed at me.

“Eehhh,” I whined at them.  “Why are you giving me the fifth degree?  I just had to tell Dean something, ok?  Something he apparently already knows!”  I still have no idea what he was talking about.  What does Charlie Bradbury know about him that I don’t already know?  I was totally buggin’.

Castiel rolled his eyes at me and stomped off.  Why?  What did I do?  This party was really starting to bum me out.  I called Sam to pick me up.  It didn’t take him long to get there, and on our way out the door, I saw Cas and Dean arguing near the shrubbery.  Awww, was Cas defending my honor, even though he didn’t know what Dean and I were discussing?  He really _is_ my best friend!

***

While Cher was a sore point in the boys’ argument, they weren’t arguing over what she thought they were arguing about.  Castiel saw Dean and Cher in deep discussion while out on the dance floor.  He couldn’t control the hope that bloomed in his chest.  He was sure that Dean was coming out to Cher.  That would have been a big step in their relationship.  If Dean could at least come out to Cher, then maybe Cas could consider getting back together with him.  Too bad he was sorely mistaken.

After leaving Cher and Summer, Cas quickly found Dean where he had rejoined Charlie.  He pulled the other man aside, and with a huge gummy grin on his face, he asked, “So, did you do it?  What did she say?  She was totally cool, right?”

“Do what?” Dean asked before something  clicked in his head.  “Tell Cher that I’m gay?” He said in a stressed whisper.  “Nuh uh, no way dude.  Cher just felt the need to inform me that my ‘girlfriend’ is a lesbian.”  Dean tried for a small smile and failed.

Cas threw his arms up in exasperation.  “Don’t you think that would have been a good opportunity to tell her?”

Dean grabbed Cas by the elbow and dragged him out to the front yard.  “No.  Why would a party full of kids from our entire school be a good time to tell the most popular girl in school that I’m a cake boy?”

Cas yanked his elbow out of Dean’s grasp.  “You know what, Dean, it’s not fair!  Don’t you think I’d like to tell my best friend that I’m in an important relationship?  Or my dad?  I risked everything to be able to be who I am.  What are you risking?  Nobody in school cares.  Your parents won’t care.  Hell, your sister is bisexual!”

It was Dean’s turn to get angry.  “What relationship?  _You_ dumped _me_ , remember???”

“Yeah, because I was tired of hiding my feelings for you.  Not because I stopped loving you!” Cas exclaimed.

Dean softened at those words.  “You love me?” he asked shyly, ducking his head and kicking the ground with an expensive Italian shoe.

“Of course I do, you assbutt!”  Cas’s heart clenched when Dean looked up at him with longing in his bottle green eyes.  “But, Dean, I can’t keep doing this.  I don’t want to hide this, hide us, from the rest of the world.”

Dean’s eyes shimmered with unshed tears.  “Oh.  Well, then…I’m sorry Cas.  I’m just…I’m not ready.”

“Well, then, I’m sorry too, Dean,” Cas said quietly before turning and walking away.

Dean watched him go, regret and self-loathing battling for dominance in his brain.

***

Winter break was over about as quickly as it started, and we were all back in school.  It’s always a bummer when a vacation is over, but there was something all of us seniors were looking forward too:  Senior Prom!  Even though it was only January, prom was all anyone could talk about.  I, however, was of two minds about prom.  Yes, it was a rite of passage for every young person approaching adulthood, but on the other hand, I highly doubted Sam would want to take me.  Why would a college guy want to go to a high school prom?  Especially one who didn’t even attend his own?  There was also the fact that Amber was head of the prom committee.  Who knew what kind of tacky theme she would come up with?  The whole idea of it made me want to shudder.

Of course, Dionne and Murray would be attending the prom, and most likely be voted Queen and King.  So, a couple of weekends after we started our last semester at Bronson Alcott High found me and Di and Cas shopping for Di’s prom dress.  Once we settled on this fabulously sparkly red number that hugged Di’s curves in all the right places, she turned to us.  Her face was way too serious for someone who’d just bought a fantastic designer dress.

“Whoa, Di, what is up?” I asked, concerned.

“We spent so much time on my dress that we didn’t find prom attire for you two!” she exclaimed.

“Oh, well, I’m not going to prom,” I said.  “But we should totally find something for Cas.”

“I’m not going either,” Cas said.

“Nonsense.  Now, Cher, I know you said Sam won’t want to go, and I know Cas isn’t seeing anyone right now.  But why don’t you go together?  You always have a fabulous time, and it would be a travesty to miss your one and only senior prom.” Dionne explained, quite rationally.

Cas and I looked at each other.  “You wanna?” I asked.

He shrugged.  “Sure.  Why not?

I would have scolded him for his lack of enthusiasm as to being my date for prom; however, I too lacked the appropriate enthusiasm.  Honestly, I was super bummed that I wouldn’t get to go with Sam.  But I was not about to make him feel obligated to do something I knew he would hate.

“Wow, you two.  Your enthusiasm is positively killing me.”  Dionne said with an eye roll and a heavy dose of sarcasm.

We stuck our tongues out at her simultaneously.  Because we’re totally mature.

“Ugh!” Dionne yelled.  “You two are the worst!”

“We know.” I agreed.  “Shall we get coffee?”  I grinned at her.

“Fine.”

After coffee, we wandered around the mall a bit more, but neither Cas nor I could find anything suitable to wear to prom.  We thought it would be fun to wear coordinating outfits.  But everything I liked, he hated, and vice versa.  That has never happened to us before.  It’s like we weren’t on the same wave length anymore.  Clearly, there was something going on with Cas that he just didn’t want to tell me, and it was interfering with our best friend bond.  Jerk.

This whole thing with Cas was majorly wigging me out.  That along with whatever Dean had been talking about at the party during winter break, I felt like I didn’t know my friends anymore.  My mind was just spinning and spinning.  I decided to take a drive to try to clear my head.  Unfortunately, with so much to think about, apparently I missed a stop light.  When Daddy got the ticket a couple of weeks later, he was not happy.

“Cher, get in here!” he bellowed from his office when I got home from school one particularly wretched afternoon.

“Yes, Daddy?”  I asked sweetly.  I could tell from his tone of voice that he was not in good spirits, so I was hoping that would help.

“What is this?”  He waved a piece of paper in front of my face.  Not like I could read it with him waving it around like that.

“I don’t know, Daddy.”

“It’s a ticket, Cher.  You ran a red light?”

I shrugged.  “I don’t know.  Maybe?  I’m sorry, Daddy.  It’s just, I’ve had a lot on my mind lately.  My friends are keeping things from me and it’s bumming me out!”

“That is no excuse!  What did I tell you would happen if you got another ticket?”

“That I’d only be allowed to drive with a responsible adult in the car with me,” I pouted.  Then, inspiration struck.  “Sam is a responsible adult, right Daddy?”

Daddy sat down in his chair and nodded.  He always did appreciate my negotiation skills.  “Yes, he is.”

“So that means that I can drive with Sam in the car?”

“I suppose so.”

“Ok!  Thank you, Daddy!  I promise to pay attention to what Sam has to say and become a better driver.”

“You better!” Daddy shouted just as I ducked out of his office.

While it was kind of a bummer that I couldn’t drive myself places anymore, as long as Sam was with me, it didn’t feel so much like an impediment on my social life.  So, the next Saturday found me driving to the mall with Sam in the passenger seat.  Cas and I still needed to find our ensemble for prom.  Too bad Sam couldn’t hang with us.  He had to work at Daddy’s office, so he was going to drop me off and pick me up after his shift.  Things were going well on the drive.  I followed all of Sam’s instructions, too.  He was totally digging the ride.

“Cher, Cher!  Slow down!  I can’t believe you managed to get your license.  Your driving hasn’t gotten any better!  No wonder your dad wants me to ride with you!”  Sam was kinda turning red, his shaggy hair whipping in the breeze as I took a corner in my Jeep (totally not too fast.)

“You try driving in platforms!” I said, pouting at him.

“You can’t use that as an excuse all the time!  Pull over, let me drive.  I’d like to live to be able to take you to your prom.”

“Why, Sam Winchester, are you asking me to prom?”

“Only if you pull this car over.  Right now!”

Of course I pulled over as quickly as possible.  And if two of my tires ended up on the sidewalk, well, who could blame me?  Sam Winchester asked me to my prom!  I quickly slid out of the car and tossed the keys at him.  Several minutes later, he finally readjusted the seat and mirrors to accommodate his 6’4” frame, and we were off to the mall.

“So, were you serious?  Sam, do you really want to take me to the prom?  I mean, I know high school dances aren’t really your scene.”  I asked in all seriousness.  I did not want my boyfriend to be miserable just to make me happy.

“Of course I’m serious, Cher.  Prom is important to you.  I want to share that experience with you.” He looked away from the road long enough to smile at me.

“Thank you, Sam!”  I said, wrapping my arms around his neck and kissing his cheek.

He gently shoved my shoulder.  “Hey, now, not while I’m driving.  Do you want your dad to revoke _both_ of our driving privileges?”

I shook my head “no.”  “Ok, I won’t risk that with inappropriate PDA.  But when we get to the mall, you’re getting a giant kiss, mister!”

He didn’t look at me, but I could still see the grin that broke across his face.  Sam Winchester was totally butt crazy in love with me!  Of course, I felt the same way about him, so it worked out.

Once I made it into the mall (after several minutes of inappropriate PDA with Sam) I had to figure out how to break the news to Cas that Sam was going to be taking me to prom after all.  I didn’t want to hurt him, but I was sure he would understand.  At least, I hoped he would.  When I found him, he was in the food court with Charlie and Dean, and he seemed in much better spirits than I had seen him in lately.  That was fantastic!

“Hey guys!” I said as I joined them.

“Well, hello, Duchess,” Cas said and kissed me on the cheek.

“You’re certainly in a much lighter mood since the last time I saw you,” I said to Cas as I returned his kiss.

He shrugged.  “I suppose I am.”

“That’s great!  I do have some news for you though, and I really hope it doesn’t kill this fantastic mood.”  I said.

“What is it?” Cas asked.  He sounded more curious than concerned.

“Sam asked to take me to prom.  Is it ok if I go with him?  I mean, I know we had plans and all….”

Cas engulfed me in a big hug that lifted me off of the ground.  “That’s great, Cher!  I know you were concerned that he wouldn’t want to go.  I’m glad he’s taking you.”

“Really?  You’re ok with it?”

“Of course I am, Duchess.  Now, let’s find you a prom dress worthy of that moose boyfriend of yours.”

“Ok!”

We found me this gorgeous periwinkle blue silk number that brought out my eyes, and we found a matching tie and paisley tuxedo vest for Sam, which would be perfect because that blue would accent the blue in his green/grey/blue hazel eyes.  Of course, we’d have to drag him back later for proper fitting.  No off the rack tuxedo would fit my giant beau.

Cas and I had a great time, but we still didn’t find anything for him.  He insisted he didn’t need anything because he wasn’t planning on going.  Well, I wouldn’t hear of such a thing.  “We have to find you something, Cas.  You have to go to your senior prom.”

“By myself, Cher?  Isn’t that just pathetic, the lone gay guy at Bronson Alcott high with no date to the prom?”  The tone of his voice when he said that hid a note of bitterness that I don’t think the situation called for.

“We will find you something to wear, and I will find you a date.”  I grabbed his shoulders and turned him to face me.  “Trust me, I’m a fabulous match maker.”

“Oh really?  Didn’t you try to fix Tai up with Dean?”

“Ok, maybe that one was a bust.  But I fixed up Mr. Hall and Ms. Geist.  And now they are deliriously happy!”

“Fine.  I’ll give you that one, I guess.  But I get full veto power on whoever you pick.  _And_ you have to come shopping with me every day until we find the appropriate tuxedo.”

“Deal!” I said, shaking his hand.

***

Unbeknownst to Cher, Castiel was going to attempt to take his prom fate into his own hands.  Taking a deep breath, and against his better judgement, with shaking hands, Cas picked up his phone and called Dean.

“Hello, Dean.”

_“Heya, Cas.  What’s up?”_

“Dean…I um…Dean…I want to…”

_“Cas, is everything ok?  Your voice sounds weird.”_

Cas took a deep breath and forged ahead.  “Dean, I know we just worked things out, and I promised not to pressure you anymore…but…but…willyougotopromwithme?” he asked in one rushed breath.

_“What?”_

“Dean, will you please go to prom with me?  If I don’t have a date, Cher is going to try to fix me up and honestly, I don’t want to go to my senior prom with anyone but you.”  There, he said it.  And now, he waited for the inevitable fallout.

Cas heard a deep breath sucked in from the other side of the line before Dean responded.

_“I’m sorry, Cas.  I just…I can’t.”_

The hurt, the anger, the sadness, the weight of his own loss all came bubbling to the surface, and Cas could take it no longer.  “That’s just fine, Dean.  Lose my number.”  He hung up the phone with a resounding click.  He grabbed his jacket and decided to go see Benny.

***

A couple of weekends later, I was lounging, well, grumping was probably a more accurate description, around the house.  Cas was supposed to pick me up so we could go to the mall to continue his search for prom attire, but he cancelled on me.  And since Sam was working today, I was stuck at the house.  Daddy even confiscated my keys so that I couldn’t possibly drive without a responsible adult present.  This weekend was stacking up to be awfully, wretchedly, lame.

I changed out of my cute mall outfit and into a soft pair of jeans and long sleeved tee shirt to lounge around the house.  I was turning the sofa into my own little den when the doorbell rang.  After a few minutes, it rang again.  A few minutes later, the ringing turned into a pounding on the door.  Maybe I forgot that Lucy had the weekend off.  And maybe I also just didn’t want to be bother.  So, I continued to ignore it.  But the pounding on the door wouldn’t stop!  I hauled myself off of the sofa and plodded towards the door.  Imagine my surprise to find Dean Smith on the other side.

“Cher, can I talk to you?”  He looked surprisingly shy.  Also, he was dressed in jeans and a flannel.  No dress shirt and suspenders?  Was this even Dean Smith?  Then again, I was wearing jeans too.  I shrugged and let him in.

“What’s up?” I asked as I lead him to the living room, where the sofa was all but buried in the empty wrappers from my various snack foods.  I started randomly tidying so that we could have place to sit and chat, while Dean just watched.  “Well, don’t just stand there looking all nervous and awkward.  Have a seat.”

Dean sat down on the edge of the sofa.  He opened his mouth several times, looking quite a bit like a fish out of water.  In exasperation, I threw my hands in the air and dropped them into my lap. “Seriously, Dean!  What is going on?  You never come over.  And now you do and look like, well, that!”  I gestured loosely in his direction.

He took a deep breath, sighed, and sat comfortably back into the sofa.  “Ok, so here’s what it is.” He rubbed his hand on the back of his neck.  “So, the thing is this…”  He trailed off again.

“What is the thing?” I asked, intrigued.

“Ok, ok, ok,” he ran his hand over his face.  “So, the thing is…”

“Spit it out!”

Dean startled at my sharp words.  “I’m gay!” He finally said, perhaps a bit too loudly for how close we were sitting.

“You are???” I asked, surprised and awe struck.  “Is that why you attacked me?  Over compensating?”

“Shut up.” He said.  “But yeah.”

“Does anyone else know?”

“Just Charlie, she’s the one who helped me figure things out.”  He ran his hand across the back of his neck again.  “And, um, well, Cas.  Cas knows.”

“Cas knows?  He never told me!”

“Yeah, well, that’s because I asked him not to.”

“Oh yeah.  And I guess it wasn’t his place to tell me,” I said softly.  “Thank you for telling me.”  I smiled at him.  The gears were already grinding in my head to fix those two up.

“Yeah, well, I’m kinda not telling anyone, so if you could keep this between us for now…”

“Yes, yes of course!  I would never break someone’s confidence.”

“I know, Cher.  You’re a good person,” Dean said softly.  “I realized I had to tell you, because well, because I sort of need your advice about something.  You’ve always been a good friend to me, and I know you and Cas are really tight….”

I clapped my hands together and squealed.  “Oooh!  Do you want me to fix you up?  Because I’m totally down for that.  I’m an excellent match maker!”

“Dude, you tried to fix me up with Tai.”

“Why does everyone keep bringing that up?  My one failure!”

“That’s not the point, Cher!  And no, I don’t need you to fix me up with Cas.  I need you to help me win him back!”

I blinked owlishly at him for what had to be at least thirty seconds.  “You need me to help you win him back?  That means you were together….Wait, when were you together????”

Dean chuckled at me.  “All last summer, you know, when Charlie and I would just kind of bump into you and Cas at the mall?”

“Yeah?”

“Then.  And then again at the beginning of the school year.  We broke up again over winter break.  Then we got back together when school started back up.  But he dumped me again, and I think it’s for the last time.”  Dean sighed deeply and dropped his head into his hands.

“Oh no!  What happened?”  I slid closer to him and placed my hand comfortingly on his knee.  Gee, I hope Sam didn’t walk in on this.

Dean took a deep breath.  “You see, Cas asked me to prom, and I said ‘no.’ I’m just not ready to come out to the entire school.  I just…I can’t do it, Cher!”

I stood up from the sofa and rounded on him.  “Dean Smith!  I am seriously disappointed in you!  Since when do you care what anyone thinks of your love life?  Also, do you have _any_ idea what Castiel has been through in order to come out of the closet?  How could you do this to him?  No wonder he dumped you!”  Ok, so maybe I should have been more sympathetic, but, seriously!  Cas went through hell just for the opportunity to be who he was.  And here’s Dean Smith, who has some of the most supportive parents ever, I might add, too scared to be with the man he supposedly loves.  For shame!

“I know, Cher.  I know you’re right!  But it’s just too hard.  I just…I can’t!”

“Well, then, what exactly do you want me to do about it?  Honestly, it sounds like he had a perfectly good reason for breaking up with you.”  I sat down and shrugged.

“Oh my God.  I really blew it, didn’t I?” Dean asked in despair.

“Yeah, I’m afraid so….”  I stood up again, as inspiration suddenly hit.  “I know how you can win him back!”

“How?” Dean asked excitedly.

“Well, you have to be willing to do that one thing you don’t want to do…”

Dean dropped his head back in his hands and groaned again.  “Do I have too?”

“Desperate times call for desperate measures, my friend.  This is the only way to get him back.  Go big or go home!”  I was getting more and more excited as the idea formed in my head.

Dean’s head popped up to look at me.  “Oh God, Cher.  Just spit it out.  What are you thinking?”  He dropped his head back into his hands.

“Dean, I think you should win Cas back with an epic prom-posal!”

Dean picked his head up again and stared at me blankly.  “What the fuck is a prom-posal?”

I rolled my eyes at him.  “Duh, it’s like, an epic extravaganza where you invite Cas to the prom in a super cute and fun and _public_ way.”

“Can’t I just, you know, _ask_ him to the prom?”

“Dude, he dumped you because you don’t want to acknowledge your relationship publically.  What better way to win him back than to publically ask him to the prom in the most epic way possible?”  I’m pretty sure my voice was speeding up and I may have reached supersonic levels, but I was so stoked about this idea!

“But Cher, I can’t.”

“Yes, you can.  And he knows this is a huge step for you, so he’ll have no choice but to welcome you back into his loving arms!”  Dean stared up at me looking a bit like a deer in the headlights.  “Ok, fine, how about this:  Let me come up with an epic prom-posal for you, and if you hate it, then you can just ask him to the prom in a private, boring way.”

“You’re not going to let up until I agree to this, are you?”

“Nope.”

“Fine.”

We chatted for a bit more about possible things Dean could do, what he absolutely would not do, and possible wardrobe choices.  Before long, I realized that Sam would be here soon, and he would not be happy to find Dean and me hanging out alone.  Hey, he doesn’t know that Dean’s not into girls!  So, I escorted Dean out.  As I let him out the front door, I said, “Don’t worry, Dean.  Leave it to me and you’ll have Cas back in no time!”

“Thanks, Cher.”  He gave me a brief hug before heading out to his car.

I sat back down on the sofa, turned the TV on to MTV in time for _Beavis and Butthead_ and let my mind wander to various ideas I could use to help Dean ask Cas to the prom.  This was going to be my best project yet!  Castiel Shurley was very particular about certain things, so everything would have to be just right.  I already had a wardrobe in mind for Dean; I just had to figure out what, exactly, he was going to do.  The hardest part was going to be figuring this out without being able to brainstorm with anyone, because it would blow the whole deal if I let Dean’s secret out before the big event!

The next weekend, I insisted Cas take me to the mall so we could keep shopping for his prom duds.  Of course, I had to make sure he was prepared; I found him the perfect date!  It was taking every ounce of will power I had not to spill the beans!  I still hadn’t figured out how Dean was going to ask him, but I was feeling fairly confident that Cas would say yes.  So obviously, he had to be ready!

When we hit up the food court for our mid-shopping lattes, who should we run into but Charlie and Dean!  Because of course we would.  Now that I knew what was going on between them, I could read Cas’s reaction like a book.  His face dropped, his voice grew quieter and less gravelly, and when he came back with our coffees, he had three donuts!  Now, Cas was very particular about what he put into his body, but when he was stressed, donuts were his go to.  I realized for the first time that Cas wasn’t just nursing the loss of his mother, but also his broken heart.  Because of Dean.  I’d kill him, but that would kind of kill my prom-posal plan.

Of course, after coffee, I ended up with a less than lackluster Castiel trying to find a tuxedo for a prom he was less than enthused to attend. What was I going to do? It took quite a bit of effort to even convince Dean that a very public prom invite was the way to go. Now, if I can’t even get Cas into a tux, what was I going to do? When Cas dropped me off at home, less than an hour later (!), he didn’t even want to come in to see the new sculpture Daddy acquired. And he lived for art! I was feeling impotent and out of control, and I really hate that.

Dean showed up a couple of hours later, presumably after he and Charlie were finished at the mall, and he also looked miserable. Currently, we were chilling in my room. He was lying on my bed, across the center, on his back with his head hanging off of the side. That wouldn’t be very good for his hair, if it wasn’t so short. Meanwhile, I was in my closet organizing my shoes into “donate” and “still in style” piles.

“Did you see him, Cher? He looked absolutely miserable. And it’s all my fault!” Dean lamented for what had to be the hundredth time in, like, fifteen minutes.

“Of course it is, Dean.” There was no sense in lying to him. “The real question is: why aren’t you talking to your own best friend about this, instead of his.”

Dean did have the audacity to look sheepish when I turned my head to look at him. “Because Charlie is tired of hearing about it. She says that since I know what to do to fix it, that I should just fix it.”

“Well, duh,” I responded.

“I know, I know!” Dean groaned as he rolled over and rearranged himself on my bed so he was buried in my pillows. “I’m just…I’m not ready yet!”

“Well, you’re going to have to get ready, and soon,” I said as I trotted over to sit next to him on the bed. “Because I figured out when you’re going to ask him.”

“What? When?” Dean asked, just barely lifting his head from the pillows.

“Ok, so, you know how I’m throwing this lavish engagement party for Dionne and Murray at the Regent Beverly Wilshire?”

“Uh-huh…”

“Well, my friend, you are going to prom-pose towards the end of the party, in front of Cas and everyone that’s anyone at Bronson Alcott High!” I exclaimed with a flourish. It was one of my best ideas yet.

Dean seemed apprehensive. “Won’t that be like stealing Dionne’s thunder?”

“Nuh-uh, no way. Why do you think I’m waiting until the end of the party? By then Di and Murray will either be celebrating their love in their own private room…ew…or fighting in the bathroom. Either way, no thunder will be stolen!”

“But that’s in two weeks, Cher!”

“I know, Dean!” I mocked. “And prom is only two months away. Cas needs time to get a tux, since he refuses to let me pick one out for him because he’s ‘not going.’ You need to ask him in plenty of time to shop!” I swear, boys could be so dense sometimes!

“But Cher, what if I just…can’t?” Dean seemed really scared.

I put my hand on his shoulder in a comforting gesture. “You can do this, Dean. The Dean Smith that I know has never let anything scare him, ever. You want to be with Cas, right?”

“Of course I do.”

“Well, then this is what you need to do. He’ll be totally floored by the unexpected romantic gesture and fall in love with you all over again. And the best thing is, he can share you with the people he really cares about! Dean, when you’re in an important relationship, it’s good to be able to introduce him to your parents.”

“My parents will freak out,” Dean said.

“As if! Isn’t your sister dating a girl?”

“That’s different.” He said sullenly.

“How?”

“Because she’s a girl?” He said that more like a question than a statement.

“You’re an idiot.” I said by way of response. Then I happened to glance at the clock. “Oh, Dean, you gotta go. Sam will be home any minute now, and well, he kinda hates you.”

“What? Why?”

“Um, you did kind of sexually harass me and leave me to get robbed at gun point. I mean, I’ve forgiven you, but I’m not sure Sam will….”

“Ugh, fine. Apparently everything I do is wrong. Later, Cher.” He slammed my door on his way out.

Shit. I didn’t mean to upset him more than he already was. Dammit.

Well, apparently Dean forgave me a couple of days later when he came over to my house, super excited.

“Cher! I’ve got the perfect way to do the prom-posal!” he exclaimed.

“Ok, stud, let’s hear it,” I said, totally not sure what to expect. I also didn’t want to tell Dean that I had an idea too. Let’s see what he came up with first…

“Ok, so get this: I buy a box of donuts from that place that Cas likes in the mall, and I write on the inside of the box, ‘I donut know if you’d want to go to prom with me, but it would be sweet if you did!’ And then I give him the donuts.” He was looking extraordinarily pleased with himself. Unfortunately, I would have to burst his bubble.

“What are you, twelve? We’re doing this at a party at a super fancy hotel. You do not bring donuts for that kind of event. Here’s what we’re going to do: I’m going to have a sign made at this great sign shop that all the hottest PR people use. The sign will simply say: Cas, will you go to prom with me?  That’s it. That’s all you need.” I was pretty proud of myself for being able to arrange this.

Dean pouted at me. He actually _pouted_. “Cher, I thought this was _my_ prom-posal. Won’t it just be enough to let Cas know that I want to take him, that I want to be seen at school with him, that I want to go public with our relationship? Shouldn’t that be enough?”

“Oh, Dean, sweetie, no. Go big or go home, right?”

“Right, sure.” Funny, he didn’t sound sure.

A few days later, I was scoping out the ballroom I booked for Di and Murray’s engagement party. I already knew how I was going to have it decorated to truly celebrate their big day. I had their prom picture from last year blown up, tastefully, to hang above the punch bowl and ice sculpture. There were going to be white and gold balloons everywhere, and streamers and twinkle lights all up and down the banister. That’s right, this ballroom had a staircase with a small balcony overlooking the dancefloor. That was where I was going to have Dean execute his prom-posal. He was going to stand up there with this amazing sign and invite Castiel to the prom, and it was going to be epic! My heart was bursting, I was so excited.

***

Of course, there were things happening that Cher just didn’t know about. For instance, the day Dean swallowed his fear and called Castiel. Who didn’t answer.

“Um, hey, Cas. It’s me, Dean. But you probably know that, that’s probably why you’re not answering. Can you give me a call back soon, before I lose my nerve? I have something to, um, ask you.”

Cas was at the bar hanging out with Benny when he finally listened to the voicemail. Benny heard it and refilled his whiskey. “Listen, brotha, I know it ain’t any of my business, but maybe you ought to give that boy a call back. At least hear what he has to say.”

“I’ll think about,” Cas assured Benny. Even though he already thought about and decided not to call Dean back.

Of course, that option was ripped from his hands when he got home that night to find Dean Smith, standing on his porch, holding a dozen red roses. “Dean, what the hell are you doing?” Castiel asked without preamble.

“Well, hello to you too, Grumpy,” Dean answered with a cheesy smile.

“Hello.” Cas said with no absence of snark. “Now, what the hell are you doing here?”

Dean practically beamed at him, actually beamed at him. “These are for you,” he said as he attempted to hand Cas the roses.

Cas shoved them away. “Why?”

“Please, Cas, can we talk?” This time Dean’s smile was smaller, sadder, but genuine.

“I guess,” Cas reluctantly agreed, as he tried, unsuccessfully to unlock the door with inebriated fingers. Dean cupped his hand around Cas’s and helped him guide the key in and open the door. “Thanks,” Cas said begrudgingly.

Not releasing Castiel’s hand, Dean led them over to the sofa, sat down, and pulled Cas down with him. “Cas, I’m so sorry. I’ve been stupid, and I’ve been scared, and I’ve been selfish. But I want to not be those things anymore.”

“Dean, could you make a little more sense? I’ve had quite a bit to drink tonight and I’d really like to go lie down.” Cas said.

Dean let go of Cas’s hand, and set down the flowers he was still holding in his other hand next to him on the sofa. He propped his elbows up on his knees and dropped his head into his hands. “I’m sorry, Cas. I know I’m not making any sense. It’s just, this is really hard for me to say.”

“Well, Dean, usually the best way to say something is to just, well, say it.” Cas grumped. He was absolutely in no mood to put up with Dean Smith’s bullshit tonight.

Dean took a deep breath and picked his head up, and turned slightly so he could look Castiel in the eyes. He took Cas’s hand, directing him to face Dean, and finally said, “Castielwillyougotopromwithme,” all in one breath.

Castiel blinked his ocean blue eyes several times as he slowly sobered up, Dean’s words starting to sink in. “Wait a minute, say that again?” Cas wasn’t sure if this was a whiskey induced hallucination or what.

Dean took another deep breath. “Castiel, will you go to prom with me? Please?”

Cas blinked at him several more times before exhaling on a sigh, “Dean, are you serious?”

“Yeah, Cas I am. I really, really am.” He looked away and rubbed the back of his neck nervously.

“You do realize that you just asked me to prom, where we will be dancing and acting coupley in front of the entire school, right?”

“Yes, Cas, I know! Alright! I know!” Dean stood up suddenly, he was shouting now, and he was starting to doubt this whole entire thing.

“Well, then, I accept. I would love to go to prom with you, Dean Smith.” Castiel smiled at him before grabbing his wrist and pulling him back down onto the sofa. “What inspired this?” He couldn’t help but ask the other boy.

Dean took another deep breath. “Well, Cas, I-I just missed you. And I talked to Charlie and Cher…”

“Wait, you talked to Cher?”

“Um, yeah. Anyway, they both said that if I wanted to have any right to call you my boyfriend, I needed to man up and deal with my issues.” He took both of Cas’s hands in his and turned to face him again. “The thing is, Cas, is that I love you and I want to be with you. I’m still worried about coming out, but none of that matters if I get to be out with you.” His smile was hopeful as he looked at Cas.

Cas wrapped his arms around Dean in a warm embrace. “Yes, Dean, as long as you are willing to try, I want to be with you.” He kissed Dean tenderly on the lips. When they parted, Cas chuckled slightly. “I still can’t believe you talked to Cher.”

“Yeah. She suggested I do this super elaborate prom-posal at Dionne and Murray’s engagement party. She even planned the whole thing. But Charlie suggested that you and I would be more comfortable discussing it this way.”

Cas chuckled again. “Well, Charlie is right. Buuut, if you don’t go along with Cher’s plan, she’ll be devastated. So you should probably just suck it up and make it happen.”

“Oh noooo!” Dean whined and dropped his head back into his hands. After a couple of minutes, he looked up again. “There really is no way to get out of this, is there?”

“Nope, I’m afraid not,” Cas laughed again.

“Son of a bitch!” Dean said. “Guess this means we have to pretend to still hate each other until the party?”

“Yeah, Dean, I’m afraid so….Unless….” Cas dragged out the word.

“Unless what?” Dean sounded hopeful.

“Unless you want to be the one to tell her that she doesn’t get do her epic thing that she’s been planning for, what, weeks?”

“Yeah, weeks. Ugh, you’re right, she’ll be devastated if she doesn’t get to do it.”

Cas shrugged. “That’s the way love goes.” He was more proud than he should have been that he pulled out the Janet Jackson lyric for this occasion.

“Well played,” Dean congratulated him. “Well played.”

Dean and Cas made out on the sofa for several minutes (hours) until it was almost past Dean’s curfew. His parents were actually home this weekend, so he had to be home on time.

***

You can just imagine how stoked I was to get a call from Dean throwing himself whole-heartedly into my prom-posal plan!  He was giving me full range, right down to even picking his outfit out! This was going to be the best prom-posal ever! My day got even better when Cas showed up to take me to the mall. He finally wanted to get a tux for the prom. I really had to give myself snaps for all the good deeds I was doing. I was helping my friends to be deliriously happy, and it was awesome.

The day of the party finally arrived, and Dean was at my house where I was helping him get ready. Sam was working late at Daddy’s office, so he was going to meet me at the hotel later. I wasn’t at all nervous about what he would show up wearing, but that’s only because I picked something out for him, laid everything out, and gave him very specific instructions on how he should appear at this party. Anyway, for some reason Dean was nervous again. We’d spent this entire week planning this to the letter, and he was fine. Now, he was dangerously close to a panic attack, and I had to intervene.

Dean leaned against the kitchen door. Even though he was nervous, I had to give myself props, he looked ultra-distinguished in his tux.  I finally got him out of the suspenders, and he was quite dapper.

“Are you sure this is going to work, Cher?”

“No doubt!  Now, do you want to win Cas back or not?”

He nodded and mumbled, “Yeah.”

“Then this is how to do it.  This prom-posal is going to blow his mind.”

“I’m just not sure I’m ready for this, Cher.  The whole school is going to find out that I’m into dudes.”

“It’ll be fine.  No one cares who you date, as long as you’re happy.  I just want to see you settled already.  Now, let’s go.  Your prince is waiting.”

The party was a success. Everyone was stoked to celebrate Dionne and Murray’s engagement. As I predicted, about two and half hours into the festivities, the couple of honor disappeared. Honestly, I didn’t really want to know if they were fighting…or, you know, the other thing. But at least if it was the other thing I wouldn’t have to talk Dionne down from trying to dump Murray. Again. I caught Summer’s eye, and she ran over to where I was. I had briefly explained my plan (without outing Dean) and asked Summer to be on Dionne and Murray patrol. When she confirmed that they were doing “the other thing,” I commenced “Operation Prom-Posal.”

I excused myself from Sam, who was actually chatting with one of the cater waiters anyway. If I rolled my eyes at him, he didn’t notice.  I collected Dean from the other side of the room, and ushered him up to the balcony overlooking the dance floor. I had stashed the banner behind the fichus up there, and much to my relief, no one had touched it.

“Alright, Dean. It’s show time. Are you ready?”

 “No.”

“Too bad!” I smiled at him as I shoved the banner into his hands. “Now, I’ve got to go get Cas and make sure he’s looking up here. You know your cue, right?”

“Yeah, you’re going to announce that I have something to say. It’s pretty hard to avoid, Cher.”

I laughed. “You know I did it that way on purpose, right? This way, you can’t back out.”

“Yeah, I know. You do know that you’re a little bit evil, right Cher?”

Oh yeah, I knew. I just nodded at him as I headed down the stairs.

I found Castiel in the corner, chatting with Charlie and Summer. I gently gripped him by the wrist and lead him to the center of the room. “Stand here and face this way.” I faced him towards the balcony. Then, I meandered over to where the DJ was and snagged the microphone he had waiting for me.

“May I have your attention please?” Suddenly all eyes were on me. It was show time! “If I may direct your attention towards the balcony, Mr. Dean Smith has something he would like to say!”

To my astonishment, Dean dropped the banner perfectly, and on cue. I had printed on it, in giant glitter letters, “Castiel Shurley, Will You Go to Prom with Me.” I managed to make my way back to Cas just as the banner was dropping. His slack jawed reaction was exactly what I was hoping would happen. He looked over at me, then back up at Dean. I nudged his shoulder with mine. “Well, go get your man!” He didn’t need to be told twice. Castiel bounded up the stairs and engulfed Dean in a giant hug. I was so proud of myself!

Sam found me shortly thereafter and pulled me aside. “Dean is gay? Why didn’t you tell me Dean is gay?”

“Um, because it’s none of your business?”

“But, but this explains everything!”

“Oh, what, so now that he’s gay you’re OK with me being friends with him? Sam, get over it.” But I wasn’t really that mad. I understand why Sam had issues with Dean. I gave Sam a peck on his cheek to show him that I wasn’t that upset with him.

“Well, after what he did, I was just surprised that you forgave him is all,” Sam said sheepishly.

“Sam, he apologized. What kind of a horrible person doesn’t accept a sincere apology?”

Sam nodded. “You’re right, Cher. You are a good person.” He pulled me into his arms and kissed me sweetly. And no, we weren’t about to go up to our own room to “do the other thing.”

Fast forward to the new school week: Apparently, Dean’s little show of bravery was inspiring to the rest of the student body. There were prom-posals all over campus. Nerds asking out cheerleaders, jocks taking their chances with bookworms, you know, the whole John Hughes experience. One particular one did manage to catch even me by surprise. One day, we were hanging out on the patio, having lunch as usual. It was me, Di, Murray, Cas, Dean, and Charlie. For some reason, Summer was running late. Well, it turned out the reason she was late was that Summer had a prom-posal of her own planned.

Before we even knew what was happening, here she came, strutting down the quad carrying that stupid snowman from last year’s Val party in one arm, like a security blanket, and a megaphone in the other. She stopped a little ways from our table and dropped to one knee, totally ruining her brand new knee highs, that I helped her pick out, and said into the megaphone, “Charlie Bradbury, would you do me the honor of accompanying me to prom? Please?”

Wait, what? First of all, how did Summer know that Charlie was into girls. Second of all, since when was Summer into girls? I was a bit stunned, but I overcame it quickly to watch my two friends share an embrace. I take it that Charlie accepted. I couldn’t help the smile that lit up my face. All of my friends were finding their happy endings, and it was the most beautiful thing ever.

Despite all of the happiness surrounding me, I just couldn’t sit back and enjoy it. There was something that was still weighing heavily on my mind, and I simply couldn’t partake in all of the pre-prom preparation and jubilation. Saturday rolled around, mall day, and some of my friends still needed prom threads. Instead of joining them at the mall, I was sitting listlessly in front of the television. I don’t know if I was watching _Ren and Stimpy_ or _Beavis and Butthead_ , or the news. I was just…staring. I totally thought I was home alone, until Sam plopped down on the couch next to me. I totally didn’t jump or squeal…well, maybe a little bit…

“Sam! What the hell? You scared me to death. Aren’t you supposed to be at Daddy’s office?”

Sam shrugged. “Probably. But it looks like you could use some company.”

“Won’t you get in trouble? Your intership and all…”

“What’s he going to do? Fire me? Besides, Mel loves me.”

“Yeah, and you’re lucky about that, because he does have a .45 and a shovel,” I chuckled at my own joke.

“Don’t think you’re fooling anyone by cracking jokes.”

“What do you mean?” I asked Sam innocently.

Sam sighed. “Look, I know you, Cher. Probably better than anyone. Something is wrong. Talk to me, maybe I can help.”

“Nothing’s wrong. You don’t know me!” I pouted and flopped further into the furniture.

“It’s Saturday, your friends are all at the mall getting ready for prom, and you’re sitting here not watching _Ren and Stimpy_. It’s your favorite show. ‘They’re way existential,’ remember?”

I sighed. “Ok, fine. It’s just that…you know…I haven’t heard from any of the colleges I applied to. It’s almost the end of my senior year, and I don’t know where I’m going to college!” I threw myself into his lap dramatically, even though I swear, I wasn’t being overly dramatic at all.

Sam wrapped his strong arms around me. “Oh. I understand, that can be unsettling. You have to remember, you just started your applications at the beginning of the school year. Most people have their applications in during their junior year.”

I sat up and looked at him. “How is this helping?”

“I’m just saying, you should give it a little bit more time. Look at it this way, you haven’t gotten any acceptance letters, but you haven’t gotten any rejection letters either, right?”

“Yeah….”

“So, there’s still hope. Even if you can’t enroll in the fall semester, you can always start in the spring. It’s no big deal. You’ll get in, I promise.”

“I hope so. What will happen to me if all my friends go to college and I don’t? You’ll dump me, obviously, because I’m so not smart enough for you. Dionne and Murray will get married and forget about me. Cas already got into San Francisco state, where he and Dean will go be happily gay together. It will just be me, alone, here, taking care of Daddy, who doesn’t even need me anymore since he started dating that lawyer lady at his firm!” If anyone asked, I did not dissolve into incomprehensible sobbing. Not me, not at all. At least Sam was still with me, for the time being. He held me close until my not-sobbing stopped.

Sam stayed with me all weekend, he tried his best to convince me that I would get into college, but I was having difficulty believing him. I felt lost and insecure. Usually, I knew where I was going and what was happening, but the real world was so much bigger and scarier than high school, and high school was coming to a screeching halt in just a couple of months’ time. I was freaking out, and there was nothing I could do to stop it.

That week, I was merely going through the motions, going to class, chatting with my friends, pretending to be excited for prom. But it was all pointless, useless, none of it was real. None of it really mattered. We were all careening into adulthood, and no one else seemed to realize it was a pretty huge deal. It was as if they all had their entire lives figured out and I was the only one who didn’t. Wait, was I the only one who didn’t?

Friday rolled around, and it was as if a sliver of light had finally penetrated my ever present cloud of darkness and despair. I had college letters in the mail! Realistically, I was fairly certain most of them were rejections, but I couldn’t control that teeny, tiny ray of hope that maybe, just maybe, I was accepted into college. To make my day even better, Sam was already there waiting for me. Wait, if he was there, why didn’t he check the mail? He stood at the kitchen island making a sandwich and smirked at me.

“So, anything good in the mail?” he asked as he slathered his bread with way too much mayo.

“You saw them, didn’t you?” I asked with a smirk of my own.

“I did,” he confirmed.

“And you just left them in the mailbox, waiting for me to find them?”

“Yep.” He replied as he began to put away the remains of the sandwich ingredients. If I stared a little too long as he was bent over in the fridge, well, would you blame me?

I stared at the pile in front of me as Sam slid into a bar stool and started in on his snack. “So, are you going to open one?” he asked me, his mouth full. I crinkled my nose at him. He was lucky he was such a Baldwin.

“I-I will open one,” I said, as I looked at the pile in front of me, then back up at him, then back down at the pile. Just as Sam was about to take another bite of sandwich, I shoved the pile at him. “You do it. I can’t.”

After almost choking on his bite, (oops) Sam chuckled and nodded. He thumbed through the pile before pulling out the envelope from UCLA. It was my first choice, for many reasons. The main one being that I could stay at home and still take care of Daddy if I wanted to. Also, it’s where Dionne and Murray were going. Finally, it’s also where Sam was already enrolled. Although we both agreed that where he was already going to school shouldn’t be a factor in my decision. Ultimately, it’s the not having to leave home that made UCLA my first choice.

“That one is thick. That’s a good sign, right?” I asked eagerly.

“Yeah, usually, a thick envelope is a good sign.” Sam agreed. He tore open the envelope, and scanned over what I could only assume was the cover letter. His lovely hazel eyes were moving over the words as I waited in eager anticipation.

Finally, I couldn’t take it anymore. “Well? What does it say?”

Sam’s smile grew wide, taking over his entire face, making his eyes sparkle. “You got in! You’re going to UCLA in the fall!”

I squealed as he scooped me up in his arms. “I’m going to UCLA!”

Now that I knew I was going to my number one school, the rest of the weeks leading up to prom went by like a gentle breeze. I mean, sure, we still had finals to get ready for, but that was a problem for another day. Besides, we all already got accepted into college, so what did high school finals matter now anyway?

Finally, the big night arrived. The limo came for me and Sam first, and he immediately disposed of the champagne, much to my chagrin.

“Look, I don’t care how much Mel likes me, he will literally kill me dead if I contribute to underage drinking!”

I pouted at him. It didn’t work.

Next, we picked up Cas, who luckily had a flask hidden in his suit jacket. We made sure Sam didn’t catch us. Then we fetched Dean and Charlie, since they lived next door to each other, it was one stop shopping for them. Dean also had a flask, so we really didn’t miss the champagne by the time we got to Summer’s. Dionne and Murray decided to take their own limo. None of us argued with them.

As soon as we arrived, it was time to make our rounds before committing to a location. Well, Cas, Dionne, and I made the rounds, everyone else just hung out near the punch bowl. Weirdos. Anyway, we had to chat up the rest of our class, and check out their fashions. It came as a surprise to no one that Amber was wearing the same dress that I wore to homecoming…last year. Seriously! “Hey, Ambuler! Were you just born a fashion victim?” I couldn’t help but chide her. I really, really am trying to be a better person…but she just gets under my skin.

Di took my arm and pulled me away. “She’s not worth it.”

Cas took my other arm. “Totally. Haven’t we been over this? She’s a full on Monet. Let’s just get back to our dates, ok?”

“You do know that Dean dated her for all of five minutes, right?” I looked up at Cas and gave him my most innocent look.

“I am aware. Wasn’t that about the same time I dated you?” Cas threw his own innocent look at me.

“Touche,” Dionne said with a smirk.

“Ugh, let’s just get back to our dates before Sam does something  embarrassing,” I pleaded with my friends.

“What? Like dance?” Cas asked smugly.

“Shut up!” I said, smacking him playfully. He wasn’t wrong. It was woefully sad how much Sam could not dance.

When we made it back to where we had left our dates, Charlie looked exaggeratedly relived. “It’s about time you got back. You should have seen these three idiots, watching you like the love sick puppies they are!” She waved her hand in the direction of Sam, Murray, and Dean.

Murray immediately came to all of their defense. “You’re one to talk, Bradbury. You should have seen the two of you.” He pitched his voice high to do an impression of Summer. “Oh, Charlie, you look so pretty tonight. That color really brings out your eyes.”

Dean joined him, doing a scarily not accurate impression of Charlie. “No, Summer, you look ravishing this evening.”

“Shut up!” Charlie said, shoving Dean hard enough to almost throw him off balance. “Now that the Queen Bees have made their rounds, can we please dance?”

“Hey, who are you calling a queen?” Cas asked in mock offense.

Charlie rolled her eyes. “You and those other two, obviously.”

“She’s not wrong,” Dean added.

“Shut up,” Cas replied eloquently.

Clearly I had to do something before the name calling and hair pulling started. “You guys go dance. Sam and I are going to see what kind of lame snacks Amber and her committee of lemmings provided.” I took Sam’s hand and pulled him away from the rest of the group.

Before we even made it to the overly extravagant snack table, Sam pulled me aside. “I um…I have a surprise for you,” he said before pulling me towards the dance floor.

“Wait, Sam! What are you doing? You _hate_ to dance. You _can’t_ dance!” I protested.

“That’s the surprise,” he said as he smoothly moved me along the floor. “I…um, I’ve been practicing. Cas has been helping me.” He smiled sheepishly at me as we melded perfectly with the other dancing couples.

And I was surprised! Sam was _good_. I mean, he wasn’t blow the roof of the place good like when me and Cas dance, but he was definitely acceptable, and maybe even better than a lot of the other guys on the dancefloor. I was suitably impressed, and very moved by his efforts.

“Sam! You’re really good! You learned this for me?” I asked. I still couldn’t believe Sam would go through all that just to be able to dance with me at my prom.

“Well, yeah. Of course I did. I love you, Cher. I would do anything for you.” He shrugged and smiled as if it was obvious.

Well, it wasn’t. “You love me?” I asked, a slow smile pulling at my lips.

“What? Like you didn’t know?” Sam asked.

I shook my head. “I didn’t know. You know, I love you too,” I said, smiling up at him.

“I do now,” Sam smiled before leaning down to kiss me.

We were soon interrupted by a tap on our shoulders. Mrs. Geist was standing there. “Now, now, kids, none of that. Sam Winchester, you should know better.” Her words may have seemed harsh, but she was smiling when she said it, so we knew we weren’t really in trouble.

“Sorry Mrs. Geist,” I said.

“Yeah, sorry Mrs. Geist,” Sam added, running a hand through his shaggy hair.

We resumed dancing when Sam asked, as if out of nowhere, “Would you do that?”

“Do what?” I asked, crinkling my nose.

“Like Mrs. Geist. She married Mr. Hall, but didn’t change her name. Is that something you would do?”

I shrugged. “I don’t know, Sam. I’m still in high school. I haven’t thought about that.”

“Oh.” Sam said, letting the subject drop like a lead balloon. Which was really weird.

Eventually, Cas came around, because of course he and I had to light up the dance floor. It was our prom, we couldn’t not dance together. It made me so happy to see that while Cas and I were dancing, Sam and Dean were actually talking and getting along. I pointed it out to Cas. “Look, Sam isn’t trying to kill Dean with looks alone.”

“Guess he’s finally forgiven him,” Cas chuckled. “You know, even I can’t believe how quickly you forgave him after what he did.”

“Hey, I’m not having this argument with you,” I joked. “Dean sincerely apologized. That was enough for me.”

“Although I’m sure it didn’t hurt when he finally told you what was going on.”

“Well, yeah. Although honestly, I was a bit hurt that it took him so long to tell me. But I’m totally over it now, and so happy for the two of you.” I told Cas sincerely.

“Thank you, Cher. That means a lot to me.” Cas wrapped me in a tight hug.

“Hey, we’d better separate before Mrs. Geist breaks us up,” I chuckled.

“Yeah, I know what you mean. She did not approve of me and Dean making out near the punch bowl,” Cas said.

“Well, there is food there you know. Gross.” I teased him.

“Haha. Very funny,” Cas deadpanned.

We continued to get our groove on, and before long, Amber took the stage to announce this year’s king and queen. I knew me and Sam wouldn’t win. He couldn’t even be nominated. But apparently, that didn’t stop people from nominating me anyway.

“Hello Bronson Alcott High!” Amber said into the microphone, and it was probably the only round of applause she would ever get. “It’s that time we’ve all been waiting for, time to announce this year’s king and queen! I’m going to start by introducing you to our court. And no, I can’t be nominated since I’m head of the prom committee, and I know you are all terribly disappointed.”

One of her lemmings handed her an envelope and she opened it with unnecessary flourish. “This year, our court consists of….Murray Turk and Dionne Davenport! Like anyone is surprised there. Next up is….” I swear, she sneered at the paper in front of her. “Castiel Shurley and Cher Horowitz…of  course. Finally, we have…Dean Smith and Charlie Bradbury? Really? Way to go, new girl,” Amber sneered as Charlie and Dean took the stage next to me and Cas.

“Now, all of you voted, and these are the three couples who received the most votes. Not that some of them are even couples. Seriously? What is wrong with you people?” Amber was ranting, which was so like her. Finally, one of her minions got her under control long enough for her to announce the actual winners. “Ok, fine. Let’s see who you people picked to be this year’s prom king and queen!”

Amber tore open the final envelope, and I swear, her face was going to freeze into a permanent sneer. “Wait, this can’t be right! We can’t have a _king and king_!”

It took about a half of a second for us to figure out what was going on. Murray quickly removed Amber from the stage, wrapping his arms around her waist and physically moving her. Then Dionne and I grabbed the envelope and the microphone.

“Eeee!” I squealed. “This is so exciting!”

Dionne smiled as she read. “This year’s prom _king_ and _king_ are Dean Smith and Castiel Shurley!”

“Yay!” I said, and placed one of the crowns on Cas’s messy hair.

Charlie stood on tiptoe to put the other one on Dean. “Have fun storming the castle!” She said, and patted him on the rear.

“Well,” Dionne prompted them.

“Well what?” Dean asked.

“You have to make a speech, duh,” I said.

“Oh,” Cas said.

Dean patted Cas on the shoulder and said, “Don’t worry, Babe. I got this.” He strode confidently over to the microphone. “This is really awesome, thanks. Guess I’m out of the closet now.” He chuckled nervously. “Anyway, I think I’m going to turn this thing over to the real queen of Bronson Alcott High, Cher Horowitz, and her lovely escort, Sam Winchester. Come on up here, you Moose!”

Weirdly, Sam didn’t look confused or surprised at all, and quickly took the stage as Dean and Cas corralled everyone else off of it. He may not have been confused, but I certainly was. Well, I was until Sam dropped to one knee. I put my hands over my mouth in shock. This couldn’t really be happening, could it? I guess it really was happening, because Sam pulled a ring box out of his coat pocket.

“Cher Horowitz, you are, all at once, one of the most sincere, sweetest, most beautiful, most spoiled, and most infuriating person I have ever met. And I love everything about you. Will you do me the honor, of, at some point in the unspecified future, of marrying me?”

I stood there, frozen to the spot, hands still over my mouth. I was stunned, in the best possible way. I couldn’t say anything. I knew what I wanted to say, but I couldn’t get the words past the dryness in my throat. Sam was there, looking up at me with pleading eyes. Perfect, wonderful, Sam, just waiting for me to answer. And I wanted to. I wanted to say “yes” with all my heart, wanted to shout it from the rooftop. But all that came out, totally against my will, was, “But I’m still in high school!”

Sam laughed. Instead of looking devastated or upset, or even surprised, Sam laughed. “I know that, Cher. That’s why I said in the future. We can be engaged as long as you want. Nothing has to happen right away, except for you accepting my proposal, and this ring, that Cas helped me pick out.”

“Yes!” I said. “Yes!” I said again, as I squealed and held my hand down for him to place the ring on.

When Sam stood up, he picked me up and spun me around before kissing me soundly on my lips, like something out of a Sandra Bullock movie. Of course, it wasn’t long before Mrs. Geist broke it up. Then, Dionne took the stage again and said into the microphone, “Now that that’s done with, isn’t it time for the prom king and king to share their first royal dance?”

A loud cheer went up from the crowd, and Dean and Cas moved into the center, still wearing their crowns. Music filled the room once again.

When Sam and I returned to the dance floor, I couldn’t help but ask, “What was that all about? You hate big, gigantic, romantic productions. You rained all over my prom-posal idea for Dean and Cas.”

“Yeah, I know. And you’re right. I do hate all of this stuff. But you love it, and I wanted it to be something you would never forget.” Sam smiled at me. “I just want to make you happy.”

“Aww, Sam! I want to make you happy too.” We kissed again. Quickly this time, before Mrs. Geist could catch us.

As we moved around the room, and I took everything in, my last major event at Bronson Alcott High, before graduation, that is, and I couldn’t help but be perfectly and absolutely content. There were Dionne and Murray, having their picture taken, and being blissfully and non-dramatically in love. Summer and Charlie were laughing and dancing, the blossom of their new love fresh in the air. Finally, there was Cas and Dean, parading around in their crowns, being fully and completely accepted by their peers. Life was good, for me and for everyone that I loved. I couldn’t wait to see what was in store for us after graduation.

 


	2. Artist's Notes

 

 

 

 

 

 

 

 

Hello Readers!

 

Wasn’t this fic great? As soon as I saw that there was a Clueless inspired fic for this Bang I immediately hoped I would get to do the art for it! And I think my Author perfectly nailed Cher’s voice, so this was just a joy to read for a girl who grew up in the 90’s like me. I chose a couple of moments that are the quintessential American high-school experience for my non-american eyes, the _"Walk down the halls eyeing the guy you like"_ and _"The Prom."_ I tried to have some fun with the clothes, as they’re a big part of what makes Clueless so interesting to watch. Trying to draw tartan was definitely a challenge (as was drawing 4 profile faces!!) but where’s the fun in a bang if not in the challenge? I of course say this now… after having redrawn Cas face 4 times. :D

 

A big big thank you to my Author, to the Mods for running this Bang with so much love and to all the other Authors and Artists who participated. Y’all are awesome!

Lots of love, 

EL (aka [Heart-eyescastiel](heart-eyescastiel.tumblr.com) on Tumblr, aka goblinsundown on Reddit & Discord :) )

 

 

 

 

 

 

 

 

 

**Works inspired by this one:**

  * [Art for Still Clueless by Andromytta for the SPN Movie Big Bang](https://archiveofourown.org/works/19257241) by [Undici](https://archiveofourown.org/users/Undici/pseuds/Undici)




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